Water → HCID 121393702, compound

HRID 1480023Notes

Reaction equation

HRID 1480023 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7](=[O:19])[NH:6][C:5]=1[C:20]1[N:24]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[N:23]=[CH:22][CH:21]=1.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C=O)C>[CH2:37]([O:36][C:34]([N:6]1[C:5]([C:20]2[N:24]([C:25]3[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[CH:31][CH:32]=3)[N:23]=[CH:22][CH:21]=2)=[C:4]([CH3:3])[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]1=[O:19])=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 121393736HCID 121393736, compound

Product 1

HCID 121393702HCID 121393702, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (38 mg of a 60% dispersion in mineral oil, 0.95 mmol) was added to a solution of 4-(5-{5-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (Example 1) (300 mg, 0.73 mmol) in DMF under a nitrogen atmosphere. The mixture was stirred for 5 minutes and the resultant yellow solution was treated with ethyl chloroformate (104 mg, 0.091 mL, 0.95 mmol). The mixture was stirred for 1 h then treated with water and extracted with EtOAc. The organic phase was washed with water and brine then dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography using silica gel eluting with 25%-50% ethyl acetate in cyclohexane. The product thus obtained was freeze-dried from acetonitrile-water to afford the title compound (194 mg) a white solid.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialthen dried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography
  7. customThe product thus obtained
  8. dry with materialwas freeze-dried from acetonitrile-water

Sources & evidence

ORD record
ord-301decbf38cc4e73b792e2702997b9b1
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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